1. David Clarkson, Toronto
Seven years, $36.8 million
The former Devil and native Torontonian was heralded loudly and proudly by the Leafs when they signed him to the biggest UFA deal of the off-season, but right from the get-go – when the league made him get up and go to the press box by suspending him the first 10 games of the year for leaving the bench in a pre-season brawl – Clarkson looked lost in Blue and White. If Toronto still had an amnesty buyout to use – and if the CBA would allow them to use one (it doesn’t) – the 30-year-old would almost assuredly be looking for another place to play.
2. Stephen Weiss, Detroit
Five years, $24.5 million
Weiss was a four-time 20-goal-scorer with the Panthers when he left Florida for Detroit. Unfortunately for him and his new team, the 31-year-old struggled with a groin injury all season and finished the 2013-14 campaign with just two goals and four points in 26 games. Because Weiss was so undependable, Red Wings GM Ken Holland had to make a deal with Nashville for pivot David Legwand at the trade deadline. With four years left on his contract, Weiss is stuck in the Motor City and may face a reduced role if Holland chooses to bring Legwand back.
3. Ryane Clowe, New Jersey
Five years, $24.3 million
As a member of the Sharks, Clowe was renowned for his physical game – but players of that ilk often break down as they enter their 30s. Clowe was 30 when he signed a massive deal with New Jersey – and wouldn’t you know it, he missed 39 games this year and amassed just seven goals and 26 points. Playing on the low-scoring Devils, it seems unlikely he’ll get back to the career-best 24 goals he scored for San Jose in 2010-11. New Jersey has always found ways to employ high-energy, gritty players, but Clowe is earning far too much to play that role.
4. Bryan Bickell, Chicago
Four years, $16 million
Bickell was a revelation for the Hawks in the 2013 playoffs when he scored nine goals (including two game-winners) and 17 points in 23 games. Chicago faced a tough decision with the pending UFA last summer. Management made the choice to trade center David Bolland to Toronto to make financial room for Bickell, but the 28-year-old winger didn’t deliver this year (11 goals and 15 points in 59 games). Was GM Stan Bowman fooled by Bickell’s playoff success skating on a line with stars Jonathan Toews and Patrick Kane? Sure seems that way.
5. Mike Ribeiro, Phoenix
Four years, $22 million
Despite producing at least 51 points in each of his first nine full NHL seasons, Ribeiro has become a journeyman in recent years. So when the 34-year-old joined the Coyotes – the fourth team of his career – on a lucrative, long-term contract, skeptics wondered if he could be a real difference-maker for Phoenix. The skeptics were validated when he posted only 16 goals and 47 points in 80 games this season. Nobody has ever questioned Ribeiro’s talent with the puck, but when you pay someone $5.5 million a season, you expect more than what he provided.